Tetraalkylcuprates(III): Formation, association, and intrinsic reactivity

Journal of the American Chemical Society

Volumn 134, Issue 1, 2012, Pages 613-622

  Putau, Aliaksei ^a   Brand, Harald ^a   Koszinowski, Konrad ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL HALIDES; ALKYL SUBSTITUENT; ARYL HALIDES; CONTACT ION PAIRS; COUNTERIONS; CROSS-COUPLING PRODUCTS; CROSS-COUPLINGS; ELECTRICAL CONDUCTIVITY MEASUREMENTS; ETHEREAL SOLVENTS; FRAGMENTATION CHANNELS; GASPHASE; HOMOCOUPLING; INTRINSIC REACTIVITY; MOLECULAR LEVELS; NMR STUDIES; PREFERENTIAL INTERACTION; REDUCTIVE ELIMINATION; THEORETICAL CALCULATIONS; TRIPLE ION;

CHEMICAL REACTIONS; ELECTRIC CONDUCTIVITY; ELECTROSPRAY IONIZATION; IONIZATION OF GASES; ISOMERS; LIME; LITHIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

IONS;

ALKYL GROUP; COPPER; COPPER DERIVATIVE; HALIDE; HALOGEN; IODIDE; LITHIUM; NEOPENTYL IODIDE; TETRAALKYLCUPRATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; CROSS COUPLING REACTION; ELECTRIC CONDUCTIVITY; ELECTROSPRAY MASS SPECTROMETRY; HOMOCOUPLING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THEORY;

EID: 84855685667     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja209433j     Document Type: Article

References (91)

1. The Chemistry of Organocopper Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: Hoboken, NJ, 2009.
2. For the few cases of known stable organocopper(II) species, see: Van Koten, G.; Jastrzebski, J. T. B. H. In The Chemistry of Organocopper Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: Hoboken, NJ, 2009; pp 23-143.
3. Willert-Porada, M. A.; Burton, D. J.; Baenziger, N. C. J. Chem. Soc., Chem. Commun. 1989, 1633-1634
4. Naumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem. 1993, 105, 1555-1556
5. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-1483.
6. Whitesides, G. M.; Fischer, W. F., Jr.; San Filippo, J., Jr.; Bashe, R. W.; House, H. O. J. Am. Chem. Soc. 1969, 97, 4871-4882
7. Vermeer, P.; Meijer, J.; Brandsma, L. Recl. Trav. Chim. 1975, 94, 112-114
8. Luche, J. L.; Barreiro, E.; Dollat, J. M.; Crabbe, P. Tetrahedron Lett. 1975, 16, 4615-4618
9. Goering, H. L.; Kantner, S. S. J. Org. Chem. 1983, 48, 721-724
10. Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900-4910
11. Mori, S.; Nakamura, E. Chem.-Eur. J. 1999, 5, 1534-1543
12. Nakamura, E.; Yamanaka, M. J. Am. Chem. Soc. 1999, 121, 8941-8942
13. Nakamura, E.; Mori, S. Angew. Chem. 2000, 112, 3902-3924
14. Angew. Chem., Int. Ed. 2000, 39, 3750-3771.
15. Snyder, J. P. Angew. Chem. 1995, 107, 112-113
16. Angew. Chem., Int. Ed. Engl. 1995, 34, 80-81.
17. Bertz, S. H.; Cope, S.; Murphy, M.; Ogle, C. A.; Taylor, B. J. J. Am. Chem. Soc. 2007, 129, 7208-7209
18. Bertz, S. H.; Cope, S.; Dorton, D.; Murphy, M.; Ogle, C. A. Angew. Chem. 2007, 119, 7212-7215
19. Angew. Chem., Int. Ed. 2007, 46, 7082-7085.
20. Bartholomew, E. R.; Bertz, S. H.; Cope, S.; Dorton, D. C.; Murphy, M.; Ogle, C. A. Chem. Commun. 2008, 1176-1177
21. Bartholomew, E. R.; Bertz, S. H.; Cope, S.; Murphy, M.; Ogle, C. A. J. Am. Chem. Soc. 2008, 130, 11244-11245
22. Bartholomew, E. R.; Bertz, S. H.; Cope, S. K.; Murphy, M. D.; Ogle, C. A.; Thomas, A. A. Chem. Commun. 2010, 46, 1253-1254
23. Bertz, S. H.; Murphy, M. D.; Ogle, C. A.; Thomas, A. A. Chem. Commun. 2010, 46, 1255-1256
24. Bertz, S. H.; Moazami, Y.; Murphy, M. D.; Ogle, C. A.; Richter, J. D.; Thomas, A. A. J. Am. Chem. Soc. 2010, 132, 9549-9551
25. Gärtner, T.; Henze, W.; Gschwind, R. M. J. Am. Chem. Soc. 2007, 129, 11362-11363
26. Henze, W.; Gärtner, T.; Gschwind, R. M. J. Am. Chem. Soc. 2008, 130, 13718-13726
27. Gärtner, T.; Yoshikai, N.; Neumeier, M.; Nakamura, E.; Gschwind, R. M. Chem. Commun. 2010, 46, 4625-4626
28. Yamashita, M.; Fenn, J. B. J. Phys. Chem. 1984, 88, 4451-4459
29. Yamashita, M.; Fenn, J. B. J. Phys. Chem. 1984, 88, 4671-4675
30. Plattner, D. A. Int. J. Mass Spectrom. 2001, 207, 125-144
31. Chen, P. Angew. Chem. 2003, 115, 2938-2954
32. Angew. Chem., Int. Ed. 2003, 42, 2832-2847.
33. Henderson, W.; McIndoe, J. S. Mass Spectrometry of Inorganic, Coordination and Organometallic Compounds: Tools, Techniques, Tips; Wiley: Chichester, 2005; pp 175-219.
34. Müller, C. A.; Markert, C.; Teichert, A. M.; Pfaltz, A. Chem. Commun. 2009, 1607-1618
35. Agrawal, D.; Schröder, D. Organometallics 2011, 30, 32-35
36. Coelho, F.; Eberlin, M. N. Angew. Chem. 2011, 123, 5370-5372
37. Angew. Chem., Int. Ed. 2011, 50, 5261-5263.
38. Lipshutz, B. H.; Stevens, K. L.; James, B.; Pavlovich, J. G.; Snyder, J. P. J. Am. Chem. Soc. 1996, 118, 6796-6797
39. Lipshutz, B. H.; Keith, J.; Buzard, D. J. Organometallics 1999, 18, 1571-1574
40. Putau, A.; Koszinowski, K. Organometallics 2010, 29, 3593-3601
41. 2010, 29, 6841-6842.(Addition/Correction)
42. Putau, A.; Koszinowski, K. Organometallics 2011, 30, 4771-4778
43. James, P. F.; O'Hair, R. A. J. Org. Lett. 2004, 6, 2761-2764
44. Rijs, N.; Khairallah, G. N.; Waters, T.; O'Hair, R. A. J. J. Am. Chem. Soc. 2008, 130, 1069-1079
45. Rijs, N. J.; Yates, B. F.; O'Hair, R. A. J. Chem.-Eur. J. 2010, 16, 2674-2678
46. Rijs, N. R.; O'Hair, R. A. J. Organometallics 2010, 29, 2282-2291
47. Lipton, M. F.; Sorensen, C. M.; Sadler, A. C.; Shapiro, R. H. J. Organomet. Chem. 1980, 186, 155-158
48. Uchiyama, M.; Furuyama, T.; Kobayashi, M.; Matsumoto, Y.; Tanaka, K. J. Am. Chem. Soc. 2006, 128, 8404-8405
49. Koszinowski, K.; Böhrer, P. Organometallics 2009, 28, 100-110
50. Hunter, H. N.; Hadei, N.; Blagojevic, V.; Patschinski, P.; Achonduh, G. T.; Avola, S.; Bohme, D. K.; Organ, M. G. Chem.-Eur. J. 2011, 17, 7845-7851
51. Satterfield, M.; Brodbelt, J. S. Inorg. Chem. 2001, 40, 5393-5400
52. Zins, E.-L.; Pepe, C.; Schröder, D. J. Mass Spectrom. 2010, 45, 1253-1260
53. Gabelica, V.; De Pauw, E. Mass Spectrom. Rev. 2005, 24, 566-587
54. Carvajal, C.; Tölle, K. J.; Smid, J.; Szwarc, M. J. Am. Chem. Soc. 1965, 87, 5548-5553
55. Krasovskiy, A.; Knochel, P. Synthesis 2006, 890-891
56. Frisch, M. J.; Gaussian 03, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
57. Hu, H.; Snyder, J. P. J. Am. Chem. Soc. 2007, 129, 7210-7211
58. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
59. Leininger, T.; Nicklass, A.; Stoll, H.; Dolg, M.; Schwerdtfeger, P. J. Chem. Phys. 1996, 105, 1052-1059
60. Rassolov, V. A.; Pople, J. A.; Ratner, M. A.; Windus, T. L. J. Chem. Phys. 1998, 109, 1223-1229
61. Figgen, D.; Rauhut, G.; Dolg, M.; Stoll, H. Chem. Phys. 2005, 311, 227-244
62. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622
63. Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B 1996, 54, 16533-16539
64. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664-675
65. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, Version 3.1; University of Wisconsin: Madison, WI, 1993.
66. Ingold, C. K. Structure and Mechanism in Organic Chemistry, 2 nd ed.; Cornell University Press: Ithaca, NY, 1969; pp 428-448.
67. Kondo, Y.; Matsudaira, T.; Sato, J.; Murata, N.; Sakamoto, T. Angew. Chem. 1996, 108, 818-820
68. Angew. Chem., Int. Ed. Engl. 1996, 35, 736-738.
69. Langham, W.; Brewster, R. Q.; Gilman, H. J. Am. Chem. Soc. 1941, 63, 545-549
70. Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1-46
71. Krasovskiy, A.; Straub, B. F.; Knochel, P. Angew. Chem. 2006, 118, 165-169
72. Angew. Chem., Int. Ed. 2006, 45, 5974-5978.
73. Moret, M.-E.; Serra, D.; Bach, A.; Chen, P. Angew. Chem. 2010, 122, 2935-2939
74. Angew. Chem., Int. Ed. 2010, 49, 2873-2877.
75. Serra, D.; Moret, M.-E.; Chen, P. J. Am. Chem. Soc. 2011, 133, 8914-8926
76. Fuoss, R. M.; Kraus, C. A. J. Am. Chem. Soc. 1933, 55, 2387-2399
77. Koszinowski, K. J. Am. Chem. Soc. 2010, 132, 6032-6040
78. Schröder, D.; Ducháĉková, L.; Tarábek, J.; Karwowska, M.; Fijalkowski, K. J.; Onĉák, M.; Slavíĉek, P. J. Am. Chem. Soc. 2011, 133, 2444-2451
79. Fleckenstein, J. E.; Koszinowski, K. Organometallics 2011, 30, 5018-5026
80. Iribarne, J. V.; Thomson, B. A. J. Chem. Phys. 1976, 64, 2287-2294
81. Thomson, B. A.; Iribarne, J. V. J. Chem. Phys. 1979, 71, 4451-4463
82. Wang, H.; Agnes, G. R. Anal. Chem. 1999, 71, 3785-3792
83. Wang, H.; Agnes, G. R. Anal. Chem. 1999, 71, 4166-4172
84. Wortmann, A.; Kistler-Momotova, A.; Zenobi, R.; Heine, M. C.; Wilhelm, O.; Pratsinis, S. E. J. Am. Soc. Mass Spectrom. 2007, 18, 385-393
85. Tsierkezos, N. G.; Roithová, J.; Schröder, D.; Onĉák, M.; Slavíĉek, P. Inorg. Chem. 2009, 48, 6287-6296
86. Luedtke, W. D.; Landman, U.; Chiu, Y.-H.; Levandier, D. J.; Dressler, R. A.; Sok, S.; Gordon, M. S. J. Phys. Chem. A 2008, 112, 9628-9649
87. Karlström, A. S. E.; Bäckvall, J.-E. Chem.-Eur. J. 2001, 7, 1981-1989
88. Norinder, J.; Bäckvall, J.-E.; Yoshikai, N.; Nakamura, E. Organometallics 2006, 25, 2129-2132
89. Mori, S.; Nakamura, E.; Morokuma, K. J. Am. Chem. Soc. 2000, 122, 7294-7307
90. Yamanaka, M.; Kato, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 6287-6293
91. Pratt, L. M.; Voit, S.; Mai, B. K.; Nguyen, B. H. J. Phys. Chem. A 2010, 114, 5005-5015